CM133L Organic Chemistry Lab

1st Quarter SY 2019-2020

EXPERIMENT 09: PREPARATION AND CHARACTERIZATION OF ALKENE

Tubog, Jalil Venice B., Marilyn Miranda

1
Tubog, Jalil Venice B., CM133L/B11, School of Chemical, Biological, Materials Engineering and Sciences, Mapua
University

In organic chemistry, an alkene is an unsaturated hydrocarbon that contains at least one carbon–carbon
double bond. The words alkene and olefin are often used interchangeably (see nomenclature section below).
Acyclic alkenes, with only one double bond and no other functional groups, known as mono-enes, form a
homologous series of hydrocarbons with the general formula CnH2n. Alkenes have two hydrogen atoms fewer
than the corresponding alkane (with the same number of carbon atoms). The simplest alkene, ethylene
(C2H4), with the International Union of Pure and Applied Chemistry (IUPAC) name ethene, is the organic
compound produced on the largest scale industrially. Aromatic compounds are often drawn as cyclic alkenes,
but their structure and properties are different and they are not considered to be alkenes.
Keywords: Alkenes, Ethene, Funcional Group

INTRODUCTION
Like a single covalent bond, double bonds can
be described in terms of overlapping atomic
orbitals, except that, unlike a single bond
(which consists of a single sigma bond), a
carbon–carbon double bond consists of one
sigma bond and one pi bond. This double bond
is stronger than a single covalent bond (611
kJ/mol for C=C vs. 347 kJ/mol for C–C)[1] and
also shorter, with an average bond length of
1.33 ångströms (133 pm). Each carbon of the
double bond uses its three sp2 hybrid orbitals
to form sigma bonds to three atoms (the other
carbon and two hydrogen atoms). The
unhybridized 2p atomic orbitals, which lie
perpendicular to the plane created by the axes
of the three sp² hybrid orbitals, combine to
form the pi bond. This bond lies outside the
main C–C axis, with half of the bond on one side
of the molecule and half on the other. With a
strength of 65 kcal/mol, the pi bond is
significantly weaker than the sigma bond.
Rotation about the carbon–carbon double bond
is restricted because it incurs an energetic cost
to break the alignment of the p orbitals on the
two carbon atoms. As a consequence,
substituted alkenes may exist as one of two
isomers, called cis or trans isomers. More
complex alkenes may be named with the E–Z
notation for molecules with three or four
different substituents (side groups). For
example, of the isomers of butene, the two
methyl groups of (Z)-but-2-ene (a.k.a. cis-2-
butene) appear on the same side of the double
bond, and in (E)-but-2-ene (a.k.a. trans-2-
butene) the methyl groups appear on opposite
sides. These two isomers of butene are slightly
different in their chemical and physical
properties.
MATERIALS AND METHODS
1st is the preparation of cyclohexame which is
assemble the setup and weigh the accurately
6.0 mL of cyclohexanol in a quick fit one necked
pear shaped flask using 2 mL pipet measure
1.50 85% phosphoric acid and add it to the
weighed cyclohexanol add 0.25 mL
concentrated sulfuric acid. Mix the reagents
using stirring rod and switch the heat regulator
to 5 or 6 end allow the mixture to distill until
0.50 mL of the mixture is left in the pear shaped
flask transfer the hydrocarbon layer of the
distillate using the pipet into a test tube. And
wash the hydrocarbon layer with 2 mL of cold
water and dry the hydrocarbon layer with 2
small pieces of anhydrous calcium chloride for 5
minutes with occasional shaking and allow the
 CM133L Organic Chemistry Lab
1st Quarter SY 2019-2020
solid to settle down and pipet liquid portion and are broken apart at high temperatures, often in the
transfer if to the 25 mL quick fit round bottom presence of a zeolite catalyst, to produce a mixture of
flask or filter using quick fit filter. The using the primarily aliphatic alkenes and lower molecular weight
simple distiallation and weighing the distillate alkanes. The mixture is feedstock and temperature
and compute for the percentage yield. Then dependent, and separated by fractional distillation. This
testing the compound prepared by cyclohexane is mainly used for the manufacture of small alkenes (up
first is the flammability by placing 2 drops of the to six carbons).apparatus, from separatory funnels to
compound in an evaporating dish and light it countercurrent distribution equipment called as mixer
with a match record the color of the flame and settlers.[not verified in body] This type of process is
add solubility and place 2 drops of compound in commonly performed after a chemical reaction as part
a micro test tube and add 0.50 mL of water and of the work-up, often including an acidic work-up.
bromination is dropping of compound in a
microtestube of preapared 1.0 M bromine in
CCl4 until it changes as observed. Oxication is
placed 2 drops of compound in a micro test
tube and drop by drop and shake 1.0N solution
of potassium permanganate and observe place
2 drops of compound and observe
REFERENCES

RESULTS AND DISCUSSION - Wade, L.G. (2006). Organic Chemistry (6th ed.)

The preparation of cyclohexene is a little bit time - Cram, D.J.; Greene, Frederick D.; Depuy, C. H. (1956).
"Studies in Stereochemistry. XXV. Eclipsing Effects in the
consuming but as it goes it narrows down to simplified E2 Reaction1". Journal of the American Chemical Society.
versions as In the table below it is seen that the boiling
point of cyclohexene we estimated is 77.8 and the - Zweifel, George S.; Nantz, Michael H. (2007). Modern
theoretical yield is 4.14 and weight of cyclohexanol is Organic Synthesis: An Introduction. New York: W. H.
Freeman & Co. p. 366
5.40 and mole of cyclohexene is 0.05
- Duan, Xufang; Block, Eric; Li, Zhen; Connelly, Timothy;
Boiling point 77.8 Theoretical 4.14 Zhang, Jian; Huang, Zhimin; Su, Xubo; Pan, Yi; Wu, Lifang
of yield of
Cyclohexene cyclohexene
Weight of 5.40 Mole of 0.05
Cyclohexanol,g Cyclohexene
Actual Yield of 1.20 %yield 27.90%
Cyclohexene

The flammability test was observed is yellow orange

was produced in the flames, as for the solubility the
indication of immisciblity formed the two layers. Then
the drops of bromine in CCl4 are added to the solutions
and the reaction occurred as for the oxidation a violet
solution was formed and produced a darkbrown with
colorless liquid and lastly sulfuric acid the solution
became hot and became colorless in it color

CONCLUSION
Alkenes are produced by hydrocarbon cracking. Raw
materials are mostly natural gas condensate
components (principally ethane and propane) in the US
and Mideast and naphtha in Europe and Asia. Alkanes